Bolling first ran for elected office in 1991 for a position on the Hanover CountyBoard of Supervisors. Bolling won that office and served as a member of the Board until 1995. While a member, Bolling also served as the Chairman of the Board of supervisors.

In 1995, Bolling was elected to the Senate of Virginia in a highly contested race against twenty year Democratic incumbent Elmo G. Cross, Jr. for the 4th Senate District seat. Bolling defeated Cross by 574 votes out of 50,000 cast.[1] The district then included Caroline, Essex, Hanover, King and Queen, King William, Middlesex, counties, as well as a part of Spotsylvania County. He was unopposed in his re-election campaigns in 1999 and 2003.

As a member of the General Assembly, Bolling served as Chairman of the Joint Republican Caucus, the Virginia Republican Senatorial Committee, Chairman of the Senate's sub-committee on Health Care, the Commission on the Future of Virginia's Environment, and the Chesapeake Bay Commission.

He was inaugurated as Lieutenant Governor on January 14, 2006 in Williamsburg, Virginia, along with the other Executive Branch officers, including Democratic Governor Tim Kaine and Attorney General Bob McDonnell. Upon his re-election in 2009, Bolling became the first Virginia lieutenant governor since Don Beyer to be elected to two consecutive terms.[citation needed]

As lieutenant governor, Bolling promoted multiple programs including his September program focused on encouraging a healthy and active life, his Ending Cervical Cancer in our Lifetime program focused on raising awareness about Cervical Cancer and HPV, and his Helping Virginians Breathe Easier campaign focused on asthma awareness.

Also as Lieutenant Governor, Bolling put forth a statewide initiative, "100 Ideas for the Future of Virginia". This two year program focused on reaching out to the public for feedback and ideas through a series of town hall meetings, mailings, and an integrated web site. This program focused on promoting feedback from the people of Virginia to develop a long term strategy for addressing issues like education, transportation, public safety, health care, protecting the environment, reforming government, and more.

He was one of newly elected Governor McDonnell's first cabinet members, and was appointed as Chief Jobs Creation Officer; the first job czar. Regarding creation of the position, McDonnell stated, "I'm going to turn him into the busiest lieutenant governor in the nation."[5]

In March 2010, Bolling announced, on behalf of Governor McDonnell, $10 million in rebates for home owners and small businesses to reduce energy costs and to increase usage of solar and wind energy.[6] In June 2010, Bolling announced $800,000 from the Virginia government to James Madison University to further research in wind energy, including "turbine testing, research and curriculum"[7]

In early 2008, Bolling and then-Attorney General McDonnell struck a deal in which Bolling agreed to run for re-election as Lieutenant Governor to allow McDonnell to run unopposed for Governor in 2009, in exchange for McDonnell's support for Bolling for Governor in 2013.[8] The deal was widely known and as such, Bolling was effectively running for Governor since 2009,[9] and in April 2010, Bolling filed the necessary paperwork to run in 2013.[10] Virginia Attorney General Ken Cuccinelli, elected alongside McDonnell and Bolling in 2009, stated that he intended to run for re-election as attorney general in 2013, but did not rule out running for Governor.[11] In December 2011, Cuccinelli announced to his staff that he would run against Bolling for governor in 2013; the news went public, and in response, Bolling issued a statement accusing Cuccinelli of putting "his own personal ambition ahead of the best interests of the commonwealth and the Republican Party."[12] Cuccinelli's announcement came two days before the annual statewide conference of Virginia Republicans, at which Bolling and his staff expressed being upset with Cuccinelli's decision.[13]

In 2012, Bolling was the Virginia state Chairman of Mitt Romney's 2012 presidential campaign,[14] a position he hoped to use to curry favor from a potential Romney administration and increase his own name recognition among state Republicans.[8] Through the second quarter of 2012, Bolling had a significant edge in fundraising over Cuccinelli.[15] However, Cuccinelli had a wide lead in early polling - a June 2012 poll of Virginia Republicans showed 51% supported Cuccinelli for governor compared to just 15% for Bolling.[16] Further diminishing Bolling's hopes was a June 2012 decision by the Republican Party of Virginia's State Central Committee to determine the nominee for Governor at a statewide convention of Republicans rather than an open primary - conservatives overwhelmingly backed Cuccinelli while more moderates backed Bolling, and conservatives tend to dominate conventions.[17][18]

On November 28, 2012, Bolling announced that he was suspending his campaign. He said that "the decision to change the method of nomination from a primary to a convention created too many obstacles for us to overcome", and that he didn't want to "create deep divisions within our party."[19] He refused to endorse Cuccinelli, saying, "I have serious reservations about his ability to effectively and responsibly lead our state."[20]

After suspending his campaign for the Republican nomination, Bolling considered running as an independent, but decided against it.[21] Bolling also rejected the possibility of a write-in effort, citing an inability to raise enough money to run a successful campaign.[22] However, Bolling continued to comment on the race and the policy proposals of both the Democratic nominee, Terry McAuliffe, and the Republican nominee, Ken Cuccinelli. McAuliffe informally offered Bolling a position in his administration, although, as of September 2014, he has not been appointed to any position since McAuliffe's election.[23]